During this post I'll be referring to the pictures in this dropbox folder:
While browsing some antique shops I stumbled across this interesting set. After a bit of googling, the jumbo pen matches what many threads are calling a 1950's jumbo tourist / souvenir pen from Japan. The big guy is in pretty good shape and functions fine. The clip says "New Clip" and the nib says "Special Ideal Pen". The body feels almost like it's made of wood. The painted details have major cities in Japan labeled in English.
What really caught my eye is the tiny, gourd-shaped pen. It seems to be a part of a set with the larger one, since the painting style is very similar. Has anyone seen this thing before? A cursory google search didn't help. Of course, there are also no real "brand" markings on the pen itself. The only marking is on the nib which seems to say "WHiNPER" (really looks more like "WH|NPER", with the bar being about half-character height). That's the only brand marking I can see. (It does also say "IRIDIUM"). The body also seems to be made of the same material as the larger pen.
I tried to figure out the filling mechanism for the small pen. The nib and collar could rotate about 90 degrees and there are two orange dots that can line up. After trying for a while, something snapped and the whole nib section came out. I then fished out some rotten rubber from inside the pen. I think I may have also broken a plastic piece connected to the collar? I can't really tell very well. Does anyone know how this little thing probably used to be filled? Also, if there are any ideas for how to maybe repair it (if at all possible), I'd quite appreciate it. I'd really like to see it functioning.